Bullying among youth at school continues to be a global challenge. Being exposed to bullying may be especially hurtful in adolescence, a vulnerable period during which both peer group belonging and status become key concerns. In the current review, we first summarize the effectiveness of the solutions that were offered a decade ago in the form of anti-bullying programs. We proceed by highlighting some intriguing challenges concomitant to, or emerging from these solutions, focusing especially on their relevance during adolescence. These challenges are related to (1) the relatively weak, and highly variable effects of anti-bullying programs, (2) the complex associations among bullying, victimization, and social status, (3) the questions raised regarding the beneficial (or possibly iatrogenic) effects of peer defending, and (4) the healthy context paradox, that is, the phenomenon of remaining or emerging victims being worse off in contexts where the average levels of victimization decrease. We end by providing some suggestions for the next decade of research in the area of bullying prevention among adolescents.